


You Haunt All of My What-ifs

by bloodsigilsandpie



Category: Supernatural
Genre: Angst, Angst and Feels, Castiel in the Empty (Supernatural), Hurt Dean Winchester, Hurt No Comfort, M/M, Originally Posted on Tumblr, Suptober 2020 (Supernatural), The Author Regrets Everything
Language: English
Status: Completed
Published: 2020-10-05
Updated: 2020-10-05
Packaged: 2021-03-07 23:33:50
Rating: Teen And Up Audiences
Warnings: Major Character Death
Chapters: 1
Words: 793
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26856001
Author URL: https://archiveofourown.org/users/bloodsigilsandpie/pseuds/bloodsigilsandpie
Summary: Cas has been in the empty for almost two weeks now and Dean slips into a daydream, thinking of what he should have done.
Relationships: Castiel/Dean Winchester, Dean Winchester & Sam Winchester
Kudos: 9





	You Haunt All of My What-ifs

**Author's Note:**

> written for suptober2020  
> Day 5: Daydream

Dean Winchester was driving his car down another empty road at unearthly hours with his brother asleep on the passenger side. Like he's been doing for years now. He could feel the steering wheel gripped a little too tight in his hands. He could hear the engine and the tires. He could see the headlights illuminating the asphalt. His eyes never left the road, but he wasn't looking out the windshield.

His mind was wandering everywhere else. Thinking. Stuck in a daydream. In a loop of different what-ifs. All of them racing in his head.

Thoughts of what could have been. Of all the words that went unsaid. And all the things he wished he had done.

He was thinking of Cas.

Castiel. An angel of the Lord. Who fell. For humanity. For him.

And what did the poor angel get in return? Eternity. In the cold, nothing of the Empty. All alone.

After all the alcohol in the bunker was gone in under three days Dean took case after case making sure he didn't have time to think. Now, almost two weeks later, he was sitting in one place with no one to distract him. Guilt and pain and regret came over him like a flood.

He thought of the first time he lost Cas. To the Leviathans. He walked into the water and didn't come back. Dean had wished he had done something to stop Cas before the gate had opened. He had wished he'd listened to Cas when he was talking about the war in heaven instead of brushing it off. But Dean found him after that. And lost him again to the madness he saved Sam from.

Then he thought of purgatory. How his mind twisted the whole event. Because it was easier to think he failed than to think his angel sacrificed himself to get him out. He had wished he could let Cas know that he cared for him more than he thought. That he had forgiven him for everything.

He thought of the angel blade pushed into Castiel's chest by that reaper. Not long after he was turned human. No grace, no wings. Just Cas. Dean remembered the fear that gripped him then. And the guilt of not getting there earlier. But Cas was brought back. Only to be left behind by Dean again.

His train of thought led him to when Cas was stabbed by the Lance of Michael. As he lay there dying he said the words Dean's always been afraid of. What else could he do but stand there avoiding his eyes?

And that time Cas _really_ died. Stabbed. By Lucifer. Dean remembered standing in the heat of the raging fire that was reducing the remains of his best friend to ashes. He had lost a lot that day, but losing Cas was different. He couldn't go on. He wanted to die too.

Then Jack brought him back and Dean felt better again. Now he wishes he would have done something with the time he had then.

He thought of their fight after Rowena went to hell. How he threw all the anger towards Chuck at Cas. And how it took almost losing him for Dean to apologize. But he was still a coward. He just couldn’t say it.

Now Cas was gone. There was no changing this. No use of thinking of what he _could have_ done. No going back. All there was left to do was drive and kill along the way. Because what's the point anymore?

"Dean," Sam's voice cut through his thoughts, barely, and said, "Pull the car over."

He only just registered the words. Still in a trance-like state, he did what his brother had told.

As the car stopped on the side of the empty road, Dean came back to reality. Very slowly. He noticed that the sun had started to come out. He turned to Sam and noticed his brother was awake and looking at him with a worried expression. Finally, he realized his face was wet with tears streaming down his cheeks.

How long was he in the car? When did he start crying? Where were they now?

His eyes fixed on his brother, he blinked a few times, slowly coming back.

"Dean..." Sam trailed off sadly. Dean blinked again and choked out, "I miss him." Sam didn't say anything, still looking with sorrow-filled eyes.

"I loved him." He managed to add, before collapsing into Sam's open arms as everything he's been pushing down inside him came tumbling out.

Sam drove the rest of the way as Dean sat quietly beside him. Slipping into a happy memory this time. One that brought a soft smile to his face. It was all that kept him going.

**Author's Note:**

> I'm sorry. I know daydream is supposed to be a happy prompt. My hand slipped.


End file.
